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Palladium catalysed asymmetric alkylation of benzophenone Schiff base glycine esters in ionic liquids

  • Dae Hyun Kim
  • , Jin Kyu Im
  • , Dae Won Kim
  • , Minserk Cheong
  • , Hoon Sik Kim
  • , Deb Kumar Mukherjee

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

Asymmetric alkyl substitution of various benzophenone Schiff base substrates under biphasic conditions proceeded using optically active Palladium(II) complexes. The corresponding products were obtained in high yields but with moderate enantiomeric excess (ee) . Addition of specific ionic liquids to the reaction medium enhanced reactivity and selectivity for phase transfer catalytic (PTC) glycine alkylation. It has been found that there is an anionic influence of the ionic liquids that modify the steric environment around the enolate ion. A computer-assisted molecular design of enantioselective phase-transfer catalysis with the palladium complex and the ionic liquid has been done.

Original languageEnglish
Pages (from-to)467-476
Number of pages10
JournalJournal of Chemical Sciences
Volume123
Issue number4
DOIs
Publication statusPublished - Jul 2011

Bibliographical note

Funding Information:
Part of this project was supported by Science and Technology Department, Ministry of Korean Government and part by the University Grants Commission (UGC), Eastern Regional Office, India.

Keywords

  • Asymmetric alkylation
  • Chiral ionic liquid.
  • Phase-transfer catalysis
  • Schiff base

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